Textile oil



Patented Apr. 22, 1941 TEXTILE OIL Alfred C. Goodings,

Harry B. Marshall, and Herbert W. Lemon, Toronto, Ontario, Canada No Drawing. Application December 21, 1939,

Serial No. 1938 19 Claims.

This invention relates to improvements in textile oils. It includes oils of suitable grade and addition agents adapted to improve the composition, particularly to facilitate the removal of the oil from the textile to which it has been applied. In a preferred form of this invention, the addition agent is a diester formed by reaction of one of the hydroxyl groups of a polyhydric alcohol containing at least three hydroxyl groups such as glycerol, with a long chain fatty acid of at least 10 carbon atoms, and by reaction of a second hydroxyl group with a short chain aliphatic acid of less than 6 carbon atoms, preferably acetic acid or hydroxy acids such as lactic acid. The resulting diester alcohol is added to any base mineral oil of suitable color, stability and viscosity for use as a textile oil.

It is common practice to use oils ontextile fibers, especially wool, to facilitate their manipulation through the various operations involved in the manufacture of cloth. One of the chief limiting factors on the use of mineral oils for this purpose is a diiiiculty encountered in their subsequent removal from the textile material by customary methods of washing or scouring. An object of this invention is to provide improved addition agents by which this difficulty is satisfactorily overcome and an oil composition containing high percentages of mineral oil is pro duced which meets all the requirements of a good textile oil.

Textile oils are exposed, particularly during transportation and storage, to a wide range of atmospheric temperatures and it is also an important requirement of satisfactory textile oil compositions that no segregation of the con stituents of the blend should occur such that a non-uniform composition of the oil may arise under conditions of use. Certain oil compositions, for example, otherwise satisfactory, are rendered commercially useless due to separation and segregation of one or more constituents of the blend when the oil is allowed to stand. Similarly, exposure to reduced temperatures may result in a disturbance of the homogeneity of composition of the oil which is not reversed by subsequent exposure to normal working Itemperatures. It is a further object of this invention to provide improved textile oil compositions of satisfactory washing or scouring properties, which do not undergo segregation under conditions of use and which, even after exposure to severe winter temperatures, are readily rendered homogeneous on warming to room temperature.

It is desired by the textile industry that the oils to be applied to wool or other textile material be pale in color, particularly in the case of oils to be used on worsteds and high quality merchandise. Other requirements of a good 310,340. In Canada February 2,

Table I General Preferred range range Gravity, A. P. I 23436 25-32 Viscosity (Saybolt Universal at F.) 50-250 -175 Pour point F..' 0-50 25-35 The following example illustrates the difiiculty of removing straight mineral oils for textiles by a scouring treatment.

EXAMPLE I Wool fabric was made to contain 5% of its weight of the oil to be tested and was then subjected to a standard scouring procedure which duplicates commercial practice and which was found to give strictly comparable and reproducible data on numerous different oils and oil blends. The composition of the scour liquor used in all cases was 0.4% soap and 0.1% sodaash in water. After scouring, the residual oil in the fabric was determined by solvent extraction and was reported both as a percentage on the weight of the fabric and also as a percentage on the weight of original oil present on the cloth before scouring. The following are results for (1) an uncompounded mineral textile oil of the type used in preparing the improved textile oil compositions of the present invention and (2) olive oil, which is representative of a good textile oil:

It has now been found that by the incorporation in suitable mineral oils defined above of from about 2 to 10% of one or more of the improved addition agents of this invention, an oil is produced which can be readily scoured off from texments of a good textile oil for industrial use. In

preferred compositions of this invention the quantity of the addition agent is of the order of 5 to 7% by volume of the base oil. Larger quantities of the addition agents up to about 120% or more may be used, particularly in preparing concentrates.

The addition agents suitable for use in this invention are diesters of polyhydric alcohols having at least three hydroxyl groups, preferably glycerol, in which one hydroxyl group is esterifled with a long chain fatty acid of at least 10 carbon atoms which is preferably largely saturated and contains not more than two, preferably not more than one, double bond, and a second hydroxyl group is esteriiled with a short chain aliphatic acid of less than 6 carbon atoms, preferably less than 4 carbon atoms, such as, acetic acid or a hydroxy acid, such as lactic acid. Examples of suitable long chain fatty acids for the esteriflcation are oleic acid and the acids of naturallyoccurring non-drying oils, including the vegetable fatty oils, such as coconut, and the animal oils, such as neats-foot and lard oils, as well as mixtures of such acids, particularly the mixed acids obtained on hydrolysis of such naturally occurring oils. Erythritol and mannitol, which possess 4 and 6 hydroxy groups respectively, when partially esterifled with a long chain fatty acid and a short chain aliphatic acid in the manner described above so as to leave at least one hydroxyl group unesterifled, also provide compounds of value for use in this invention. The preparation of suitable diesters for use in this invention is illustrated by the following example:

EXAMPLE II Coconut monoglyceride is prepared by reacting coconut oil with glycerol using preferably an excess of glycerol above that required for theoretical conversion of the coconut oil to fatty acid monoglycerides. This reaction is accomplished for example by heating 100 volumes of coconut oil with 21 volumes of glycerol at about 220 C. for five hours, using small amounts of alkali :as a catalyst. This esteriflcatlon reaction does not proceed entirely to completion but reaches an equilibrium in which there are small percentages of the original reactants, namely, glycerol and coconut triglyceride. If this mixture is acetylated, the free glycerol is converted to the monoand diacetylated glycerols, which are high boiling liquids, soluble in water, insoluble in petroleum oils. The presence of these compounds in the desired coconut-acetic diglyceride is objectionable because of their insolubility in mineral oil which prevents the preparation of a completely clear textile oil solution. This difiiculty can be overcome in any one of three ways (a) The glycerol may be extracted from the coconut monoglyceride with water.

(b) The acetylated glycerol may be extracted from the coconut acetic diglyceride with water.

In either case, residual water is then removed from the extracted coconut acid ester by any suitable method as by passing a dry gas through the hot liquid with suitable agitation.

' (c) Other agents which prevent separation of the acetylated glyceride from the textile oil composition, such as, liquid diglycerides of long chain fatty acids of at least 12 carbon atoms, may be added. This will be described below. I

The coconut acid monoglyceride prepared as described above, with or without prior separation of unreacted glycerine, is then acetylated by re-' action with acetic anhydride. This is accomplished by heating the coconut acid monogiyceride product with35 volumes of acetic anhydrlde thereby providing a slight excess of the acetylating agent. There is thus obtained a glycerol diester of the coconut acids and acetic acid which is identified for the purpose of this invention as coconut-acetic diglyceride.

Similar glycerol diesters may be prepared from neats-foot oil and from oleic acid. Lactic acid anhydride may be used in place of the acetic .anhydride to prepare corresponding diesters of a long chain fatty acid and of lactic acid. Examples of suitable glycerol diesters for use in this invention are:

Coconut-acetic diester oi glycerol Neats-foot-acetic diester of glycerol Neats-foot-lactic diester of glycerol The following scouring test data illustrate the efliciency of these compounds as addition agents to mineral oils to improve ease of scouring. The compositions tested were prepared by dissolving in a mineral textile oil of the type described above, glycerol diesters in the amounts indicated in the table. The scouring test was the same as that described above in Example I.

Mineral oil/coconut-acetic diglyceride mixtures Mineral oil/neats-foot lactic dzglyceride mixtures Residual oil Composmon of 011 Percent on Percent on weight of weight oi fabric original oil 100% mineral oil 2. 25 45. 0 99% mineral oil +l% neat's-foot-lactic diglyoeride l. 38. 0 98% mineral oil +2% neats-foot-lactic diglyceride. 0. 85 i7. 0 97% mineral oil +3% neats-foot-lactic dig ycen a 0. 57 ll. 4 96% mineral 011 +4% neatsdoot-lactic diglyceri e 1 0. 52 10.4 mineral oil +5% neats-foot-lactic diglycende 0. 45 9. 0 94% mineral oil +6% neets-foot-laetic digly ceride 0. 43 B. 6 93% mineral oil +7% neat's-footdactrc diglyeende 0. 43 8. 5

Similarly, a textile oil composition containing 94% mineral oil and 6% neat's-foot-acetic diglyc- Suitableitconcentrations for the preferred textile'ioil compositions of this invention are thus apparentairom the compositions shown to meet this test inrthe'above tables of scouring test data. tThef textile 1 oil compositions described above also iindergono'segregation of any of the constituents leading to loss in scouring efllciency under any conditions of atmospheric temperatures ordinarilyjencountered, even including the extremely-lowtemperatures of northern winters.

Ifan oil issubjected to progressively decreasing temperature. it passes from a liquid to a 'gelatinousstate. 1 In the case of a mineral textile oil to'which compounds have been added to inthe ease oi scouring these addition agents on coolingthe oil blend, precipitate out irom the mineral oil while the latter is still iiquidgiiioritheoil composition to be satisfactory i'orltextiieuse, it is imperative that said solidification 'offany of the constituents brought about by reduction of temperature should not be aeco npanied by a segregation leading to such non-uniiorm composition that portions of the oil haveji ot thenecessary good scouring properties. flhe iact that one constituent may solidity before another with reduction in temperature is not in itseliimportant provided uniformity of distribution throughout the mass is not disturbed. It is further necessary that irrespective of the previous temperature conditions within the limits of atmospheric range to which the oil has been subjected, a homogeneous liquid product results when the oil. islater exposed to a temperature of 5'03 F.l,,.'rhe improved textile oil compositions of the present invention satisfy these requirements. The diestersof long chain and short chain ,acidsldeseribed above may also be used in textile oil compositions with other scouring aids such ,as the normally-;liquid monoand di-glycerides oilong chainiatty acids having at least 12 carbon atoms in the acid radical. Even though some of these normally liquid diesters tend to separate found tl'iat theymay be used with the diesters 01! long cum and short chain acids described above thattheirtendency to precipitation and segregation is thereby overcome. For example,

a no m! liquid diglyceride of neats-ioot oil scan which would itself partly settle out from solution in a textile mineral oil on cooling, will if witHneats-foot-lactic diglyceride in suitableproportions provide a mixture of diglycerides overcomes these difficulties of separation and which-fis'satisfactory for use as an addition agent in thel production of textile mineral oil comp'ositions'ln accordance with the present in- The eflect s oi' the additiono'i'neat's ioot-lactic 1 di'glyceride om-1th: precipitation or neats-ioot from solutionsin textile mineral oils, it has been diglyceride at low temperatures (5 C.) from solution in a textile mineral oil is indicated in the following table:

Composition of mizture in mineral oil Volume oi pre- 7 neat's loot 7 neats-looto a clpltation' diglyceride lactic diglyoeride Negligible Negligible Negligible Negligible The volume of precipitation is expressed in arbitrar units with the figure 10 denoting the amount of. precip tation taking Place in a 5% solution of neat's-toot diglyceride in m neral oil (5 C.) without the addition of any neats-foot-lactic diglyceride.

Exciter: m

The following table gives scouring test data which illustrate the effectiveness on ease of scouring of additions of mixtures of neats-toot diglyceride and neats-ioot-lactic diglyceride to a mineral textile oil of the type described above.

[A=oqual parts of neat's-foot-diglyceride and nent's-footlactic diglyceride] Residual oil Composition of oil Percent on weight oi tabric Percent on weight of The monoand diglycerides of the mixed fatty acids from many naturally occurring non-drying fatty oils such as neats-foot oil and lard oil are partly solid and partly liquid at temperatures from 50 to 70 F. By cold pressing, decantation, centrifuging, or other means of separating the liquid and solid portions, liquid fractions (liquid at 50 F.) of the monoand diglycerides are obtained. These liquid monoglycerides and diglycerides are preferred for use in compositions with the glycerol diesters of long chain and short chain acids described above. The solid fractions of the monoand diglycerides of oils such as coconut oil and neats-foot oil are not suitable for use in these compositions. These normally solid monoand diesters can. however, be used as illustrated in Example 11 to prepare the mixed esters of long chain and short chain acids. For example, the normally solid traction of the diglyceride made from neats-ioot oil can be employed in the manufacture or neat's-ioot-lactic diglyceride thereby providing use for the entire neats-ioot oil and permitting marked savings in the total cost oiproduction oi the addition agents. An exoriginal oil 4 ample of a suitable addition agent consisting of such a mixture of diglycerides is 1 part neats-foot diglyceride 1 part neats-foot-lactic diglyceride foot diglyceride.

isA suitable composition of the final oil mixture The foregoing description is for the purpose of illustration only and various changes and alternative compositions may be made without Per cent Mineral 94 1s Neats-foot-diglycerid 3 Neats-foot-lactic diglyceride 3 The liquid monoor diglyceride may also be used in conjunction with mixed diglycerides derived from a different oil, as in the following illustrative composition:

Per cent Mineral ofl 94 Coconut-acetic diester of glycerol 4 Neat's-foot diglyceride (liquid fraction) 2 The textile oil compositions described herein may be applied to the textile material in the usual manner as by spraying or sprinkling, either directly or after emulsiilcaticn with water. In the case of oil emulsions, the oil is ordinarily used in about two to eight times its volume of water, with or without addition of alkali to the water. To simplify preparation of such an emulsion, it is an advantage if the oil will readily mix withwater without recourse to the use of additional compoundsson the part of the textile mill operative. The addition agents discussed herein are designed primarily to improve the ease of scouring of the textile oils, whether emulsified or not, and also have the effect of improving the emulsifiability .of the textile oil compositions to some extent. Where it is required that the textile oil compositions should emulsify very readily in water, it is desirable to incorporate secondary addition agents into the oil for this purpose. Examples of suitable emulsifiers are the oil-soluble sulfonates, ethanolamines and the like. For example, about 3% of the mineral oil in any of the textile oil compositions described above may be replaced by an equal volume of triethanolamine. Fat solvents such as cyclohexanol (hexalin) may also be added to assist in keeping any normally solid diesters in solution.

Although emphasis has been laid on the use of mineral oils, it will be understood that the invention is applicable also to oils of animal and vegetable origin, for example, olive oil and lard oil. The addition of the diesters of glycerine, described herein, for example, to such oils, facilitates their removal from textile material, by scouring,\ though not to so great a degree as in the case of mineral oils.

For exdeparting from the spirit of this invention, it

being intended to claim all novelty inherent inv this invention as broadly as the prior art permits.

We'claim:

1. A textile oil comprising a base oil having a Baybolt Universal viscosity between about 50 and 250 seconds at It, and containing as a scouring assistant an effective amount of a mixed diester of a polyhydric alcohol of at least three hydroxy groups with a long chain fatty acid of at least 10 carbon atoms and not more than two double bonds and a short chain aliphatic acid of less than about 6 carbon atoms.

2. Composition according to claim 1 in which the said polyhydric'alcohol is glycerol.

3. Composition according to claim 1 in which the said short chain aliphatic acid is a fatty acid.

4. Composition according to claim 1 in which the said short chain aliphatic acid is acetic acid.

5. Composition according to claim 1 in-which,

the said short chain aliphatic acid is an hydroxy aliphatic acid.

6. Composition according to claim 1 in which the said short chain aliphatic acid is lactic acid. 7. A textile oil comprising a mineral base oil having a Saybolt Universal viscosity between about 50 and 250 seconds at 100 F. and con- .taining as a scouring assistant an effective amount of a mixed diester of glycerol with a long chain fatty acid of a non-drying fatty oil and a short chain aliphatic acid of less than 4 carbon atoms.

8. Composition according to claim 7 in which said fatty oil is neats-foot oil.

9. Composition according to claim 7 in which said fatty oil is lard ofl.

10. Composition according to claim 7'in which said long chain fatty acid is oleic acid.

11. Composition according to claim 7 in which said long chain fatty acid is obtained from the normally solid fraction of the diglycerides of the fatty acids of a non-drying fatty oil.

12. A textile oil composition comprising a mineral base oil having a Saybolt Universal viscosity between about 50 to 250 seconds at 100 F. and containing as a scouring assistant a mixture of diesters of glycerol, one di-ester being a mixed diester of glycerol with a fatty acid obtained from the normally solid fraction of the diglycerides of the acids of a non-drying fatty oil, and a short chain aliphatic acid of less than 4 carbon atoms, the other diglyceride being a normally liquid diglyceride of the acids of a nondrying fatty oil. 1

l3. Composition according to claim 12 in which said fatty oil is neats-foot oil.

14. Composition according to claim 12 in which said fatty oil is lard oil.

15. Composition according to claim 1 in which said base oil is a mineral oil having a Saybolt Universal viscosity between about and F., an A. P. I. gravity between about 25 and 32, and a pour point between about 25 and 35 F.

16. Composition according to claim 1 in which the oil is emulsified with water.

17. A textile oil comprising about 94% mineral oil having a viscosity within the approximate range of 50 to 250 seconds Saybolt Universal at 100 F., and about 6% of coconut acetic diester of glycerol.

approximate range of 50 and 250 seconds Saybolt Universal at 100 F., about 3% of a liquid neats-foot oil acid diester of glycerol and about 3% of neats-foot-lactic diester of glycerol.

ALFRED C. GOODINGS. HARRY B. MARSHALL. HERBERT W. LEMON. 

